title: Asymmetric synthesis of both enantiomers of arteludovicinolide A.
abstract: The first total synthesis of either enantiomer of Arteludovicinolide A and their biological evaluation is reported, featuring a new strategy for the asymmetric construction of γ-butyrolactones with stereogenic side chains in the 4-position. Starting from the renewable resource methyl 2-furoate, the sesquiterpene lactone was synthesized in 9 steps and 4.8% overall yield via an asymmetric cyclopropanation and two diastereoselective nucleophile additions making use of a donor-acceptor-cyclopropane-lactonization cascade. At noncytotoxic concentrations (≤10 μM) (+)-1 was found to have a 15 times higher anti-inflammatory activity (4.87 ± 1.1 μM) than previously reported for concentrations of ≥45 μM.
authors.affiliation: Institut für Organische Chemie, Universität Regensburg, Universitätsstr. 31, 93053 Regensburg, Germany.
authors.forename: Andreas
authors.initials: A
authors.lastname: Kreuzer
authors.forename: Sabine
authors.initials: S
authors.lastname: Kerres
authors.forename: Thomas
authors.initials: T
authors.lastname: Ertl
authors.forename: Hannelore
authors.initials: H
authors.lastname: Rücker
authors.forename: Sabine
authors.initials: S
authors.lastname: Amslinger
authors.forename: Oliver
authors.initials: O
authors.lastname: Reiser
mesh_terms: D015107:4-Butyrolactone / Q000737:chemistry*; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D012717:Sesquiterpenes; C585358:arteludovicinolide A; D015107:4-Butyrolactone